Ateneo - UPO

The course introduces the main theoretical and practical aspects of synthetic organic chemistry, with particular emphasis on laboratory activities.
The first part is devoted to safety in the chemistry laboratory, the correct use of laboratory equipment and glassware, and the organization of experimental work. The role of the laboratory notebook is also discussed, together with appropriate methods for documenting experimental procedures, observations, and results.
The course then addresses the main elements involved in the planning and execution of an organic reaction. The role and selection criteria of reaction solvents, the properties and proper handling of reagents, and the techniques used to work under anhydrous conditions are discussed. Particular attention is given to setting up different types of reactions, carried out at low or high temperatures and, when required, under an inert atmosphere.
The main techniques used to monitor reaction progress, work-up procedures, and methods for product isolation and purification are examined in detail. The compounds obtained are subsequently characterized using the main spectroscopic techniques.
Through the analysis of examples taken from the scientific literature, students become familiar with the structure, language, and interpretation of experimental procedures in organic synthesis. The course also includes activities devoted to the retrieval and critical evaluation of scientific information through the use of databases and bibliographic tools.
The final part of the course introduces advanced and non-conventional approaches to organic synthesis, with particular emphasis on the principles of green chemistry, microwave-assisted synthesis, flow chemistry, photochemistry, and biocatalysis.

Vogel’s textbook of practical organic chemistry, 5th Edition – B. S. Furniss; A. J. Hannaford; P. W. G. Smith; A. R. Tatchell
Advanced practical organic chemistry – J. Leonard; B. Lygo; G. Procter
Laboratory Techniques in Organic Chemistry: Supporting Inquiry-driven Experiments - Brossura, 4th Edition – J. R. Mohrig; D. G. Alberg; G. E. Hofmeister; P. F. Schatz; C. N. Hammond Practical process research and development - N. G. Anderson – Academic Press

The course aims to introduce students to the theoretical and practical aspects of organic synthesis applied to the preparation of molecules of pharmaceutical interest. Particular attention is devoted to safety in the chemistry laboratory and to the main techniques used for reaction setup and monitoring, work-up, isolation, purification, and characterization of the products obtained.
The knowledge acquired during the lectures is applied through laboratory activities designed to develop familiarity with the main operations of practical organic synthesis and with the proper documentation of experimental work.
The course also introduces the fundamental principles of retrieving information from the scientific literature and of innovative synthetic methodologies, promoting a critical approach to the selection, interpretation, and application of experimental procedures.

Physical Methods in Organic Chemistry: Knowledge of the main spectroscopic techniques, primarily IR and NMR spectroscopy, for the structural determination and characterization of organic molecules. The interpretation of the data obtained enables students to address problems related to the synthesis and analysis of the organic compounds under investigation.

The course is divided into three parts.
The first part consists of a series of lectures devoted to safety and to the main techniques used in an organic synthesis laboratory. At the end of this section, students are provided with experimental procedures taken from scientific articles, which are translated, analyzed, and discussed collectively at the board.
The second part consists of laboratory activities, during which students apply the knowledge acquired through the practical execution of a range of organic synthesis reactions.
The third part includes lectures devoted to retrieving information from the scientific literature to non-conventional synthetic techniques. One of these sessions is held in a computer laboratory, where students have the opportunity to practice literature searching using databases, scientific search engines, and SciFinder.
The lectures are supported by PowerPoint presentations, which are made available to students at the beginning of the course.

Students with physical disabilities, Learning Disabilities or Special Education Needs can request specific services and tools via the Staff Sviluppo e Coordinamento Carriere e Servizi alle Studentesse e agli Studenti, consulting the University webpage: https://www.uniupo.it/en/services/services-students-physical-or-learning-disabilities.
Students with disabilities, learning disabilities or special education needs, once they have contacted the University Staff, can refer to the tutor in charge of the course to define the examination modalities, concerning academic aspects.

Access to the laboratory is subject to passing a first written test consisting of 28 questions. Of these, 22 cover the topics addressed in the preparatory lectures, while the remaining 6 involve exercises based on a synthetic procedure written in English and taken from the scientific literature.
To pass the test, students must answer at least 16 out of 28 questions correctly.
During the laboratory activities, students are assessed on the basis of the experiments performed, the commitment demonstrated, and the results obtained.
At the end of the laboratory component, a second written test consisting of 5 questions is administered on the topics covered in the final part of the course. To pass this test, students must answer at least 3 out of 5 questions correctly.
The final grade will take into account the results obtained in both written tests and the assessment of the laboratory activities.

The course introduces the meaning and role of organic synthesis, outlining its main purposes and applications. The first part is devoted to safety in the chemistry laboratory and to the rules of conduct required to carry out experimental activities correctly. Hazard symbols, risk and safety statements, including the R/S and H/P classifications, and the main routes of exposure to chemical substances, such as ingestion, inhalation, and skin absorption, are examined. The appropriate actions to take in the event of exposure or poisoning are also discussed, together with the risks associated with toxic, carcinogenic, flammable, and explosive substances, physical hazards, and the correct procedures for the management and disposal of chemical waste.
The course then presents the main equipment used in an organic synthesis laboratory, commonly used glassware, and laboratory tools made of materials other than glass. Particular attention is devoted to the selection of reaction solvents, their influence on the reactivity and selectivity of chemical processes, and the techniques used for solvent purification and drying. The correct handling of reagents, their purification, and the methods used for their measurement and transfer are also covered.
The techniques required to work under anhydrous conditions and to set up reactions under different experimental conditions are illustrated. Topics include the heating and cooling of reaction mixtures, the use of inert atmospheres or gaseous reagents, strategies for shifting chemical equilibria, and the performance of catalytic hydrogenation reactions.
A specific section is devoted to monitoring reaction progress, with particular reference to thin-layer chromatography (TLC). The main work-up operations are then examined in detail, including reaction quenching, extraction, preliminary drying and drying of organic phases, filtration, and solvent evaporation. Examples of operational sequences and purification workflows applicable to different types of reactions are also discussed.
The course covers the main methods used for the isolation and purification of organic products, including column chromatography, crystallization, sublimation, and different distillation techniques: simple, fractional, vacuum, and steam distillation. The products obtained are subsequently characterized using the main analytical and spectroscopic techniques.
Particular attention is devoted to the correct use of the laboratory notebook and to the documentation of experimental procedures, observations, and results. Through the analysis of synthetic procedures taken from the scientific literature, students learn how to perform the calculations required to carry out a reaction and how to select the equipment and glassware appropriate to the scale and experimental conditions.
The course also includes a section devoted to the retrieval of scientific information, with particular reference to the distinction between primary and secondary sources and to the informed use of the main bibliographic resources.
The final part introduces innovative principles, technologies, and approaches applied to organic synthesis. Topics include the principles of green chemistry, phase-transfer catalysis, microwave-assisted synthesis, biocatalysis, flow chemistry, electrochemistry, and photochemistry.

Knowledge and understanding. By the end of the course, students will have acquired knowledge of the fundamental principles of practical organic synthesis and of the main operations carried out in a synthetic chemistry laboratory. They will be familiar with laboratory safety regulations, the risks associated with handling chemical substances, and the correct use of laboratory glassware and equipment. They will understand the role of solvents and reagents, the main techniques used to work under anhydrous conditions or an inert atmosphere, and the methods employed for reaction setup, monitoring, and work-up. They will also be familiar with the main techniques used for the isolation, purification, and characterization of organic products, as well as with the fundamentals of literature searching and innovative synthetic methodologies.
Applying knowledge and understanding. Students will be able to interpret an experimental organic synthesis procedure taken from the scientific literature and identify the operations required for its execution. They will be able to perform the necessary stoichiometric calculations, select appropriate glassware and equipment, set up a reaction under the specified conditions, and apply the main techniques for reaction monitoring, quenching, extraction, filtration, drying, solvent evaporation, and purification.
They will also be able to document laboratory activities correctly in a laboratory notebook and use the available analytical and spectroscopic data to verify the identity and quality of the products obtained.
Making judgements. Students will be able to critically evaluate a synthetic procedure and identify its main limitations and potential issues in terms of safety, experimental feasibility, selection of reagents and solvents, reaction conditions, work-up procedures, and purification methods. They will be able to identify the risks associated with different laboratory operations and adopt appropriate preventive measures and working practices in compliance with safety regulations and procedures. They will also be able to search for and select information from the scientific literature, distinguish between primary and secondary sources, and critically assess the reliability, relevance, and applicability of the information retrieved.
Communication skills. Students will be able to describe the experimental procedures performed, the observations made, and the results obtained using appropriate scientific language. They will be able to communicate clearly with their peers and teaching staff during laboratory activities, accurately sharing information on the operations carried out, the experimental conditions, potential risks, and any problems encountered. They will also be able to record experimental work in the laboratory notebook in an orderly and rigorous manner and discuss the results obtained using the terminology of synthetic organic chemistry.
Learning skills. Students will have acquired the tools required to independently explore organic synthesis procedures and methodologies and to undertake experimental activities of increasing complexity. They will be able to use the scientific literature and the main bibliographic resources to retrieve information on reactions, reagents, experimental conditions, purification techniques, and characterization methods. The knowledge and skills acquired will also provide a foundation for understanding more advanced aspects of pharmaceutical synthesis and the development of innovative and sustainable synthetic methodologies.